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Materials for organic electroluminescent devices

A compound and general formula technology, applied in the field of transition metal complexes, can solve the problems of impossibility, reduced transition efficiency, difficulty in pure primary color, etc.

Active Publication Date: 2011-05-25
UDC IRELAND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These aggregates often have irregular broad emission bands that make the generation of pure primary colors (RGB) rather difficult or impossible
Overall, the transition is also less efficient

Method used

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  • Materials for organic electroluminescent devices
  • Materials for organic electroluminescent devices
  • Materials for organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] Embodiment 1: the synthetic steps of metal complex (1)

[0114]

[0115] Step 1: Ligand Synthesis

[0116] The ligand synthesis was carried out using azeotropic distillation to remove the water formed. First, 300 ml of dry toluene was heated to boiling in the distillation apparatus of a 500 ml three-necked flask with stirrer, internal thermometer and dropping funnel. A solution of 20 g (120 mmol) of 2-diphenylamine in 50 ml of dry toluene and a solution of 21.9 g (120 mmol) of 6-phenylpyridine-2-carboxaldehyde in 50 ml of toluene were then slowly added dropwise and sequentially. To this mixture is added a catalytic amount of p-toluenesulfonic acid. Distillation was carried out until clear condensed toluene appeared. Residual solvent was removed in oil pump vacuum (130 Pa). The ligand was recrystallized from toluene and washed with MeOH to afford 31.5 g (94 mmol) of a crystalline solid. The overall yield was 80%.

[0117] Step 2: Complex Synthesis

[0118] The ...

Embodiment 2

[0119] Embodiment 2: the synthetic steps of metal complex (8)

[0120]

[0121] Step 1: Ligand Synthesis

[0122] The ligand synthesis was carried out using azeotropic distillation to remove the water formed. First, 300 ml of dry toluene was heated to boiling in the distillation apparatus of a 500 ml three-necked flask with stirrer, internal thermometer and dropping funnel. A solution of 20 g (120 mmol) of 2-diphenylamine in 50 ml of dry toluene and a solution of 21.9 g (120 mmol) of 3-pyridin-2-ylbenzaldehyde in 50 ml of toluene were then slowly added dropwise and sequentially. To this mixture was added a catalytic amount of p-toluenesulfonic acid. Distillation was carried out until clear condensed toluene appeared. Residual solvent was removed in oil pump vacuum (130 Pa). The ligand was recrystallized from toluene and washed with MeOH to afford 30.1 g (90 mmol) of a crystalline solid. The overall yield was 76%.

[0123] Step 2: Complex Synthesis

[0124] The 1300ml...

Embodiment 3

[0125] Embodiment 3: the synthetic steps of metal complex (30)

[0126]

[0127] Step 1: 8-nitro-2-naphthylquinoline

[0128] Suspend 18.9g (110.0mmol) 1-naphthylboronic acid, 22.9g (110.0mmol) 2-chloro-8-nitroquinoline and 44.6g (210.0mmol) tripotassium phosphate in 500ml toluene, 500ml dioxane and 500ml of water. 913 mg (3.0 mmol) of tri-o-tolylphosphine were added to the suspension, followed by 112 mg (0.5 mmol) of palladium(II) acetate, and the reaction mixture was heated to reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and evaporated to dryness. Yield 26.4 g (87 mmol), corresponding to 80% of theory.

[0129] Step 2: 8-Amino-2-naphthylquinoline

[0130] 12.6 g (42 mmol) of 8-nitro-2-naphthylquinoline and 1.99 g of Pd / C (10%) were suspended in 200 ml of methanol. 8.4 g (222 mmol) of sodium borohydride were added portionwise with stirring at 0°C. After stirring for 2 h, the c...

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PUM

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Abstract

The present invention relates to transition metal complexes of the general formulae (I) or (II), in particular as emitter molecules in organic electronic devices, a layer and an electronic device which contain the compounds according to the invention as well as a method for producing the compounds according to the invention.

Description

technical field [0001] The invention relates to transition metal complexes of the general formula I or II, in particular for use as light-emitting molecules in organic electronic devices, to layers and electronic devices comprising the compounds according to the invention, and to processes for the preparation of the compounds according to the invention. Background technique [0002] Chelates and organometallic compounds are used as functional materials in many different types of applications, which can be attributed to the electronics industry in the broadest sense. Market introductions have already been made in the case of organic electroluminescent devices based on organic components (for a general description of the structure cf. US 4,539,507 and US 5,151,629) and their individual components, the organic light-emitting diodes (OLEDs). Although success has been achieved, further improvements are still needed here. [0003] In recent years, organometallic complexes with ph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F15/00H05B33/14H01L51/00H10K99/00
CPCC09K2211/1022C09K2211/1029C09B55/003H01L51/0087C09B57/10C09K2211/185C09B57/00H05B33/14C09K11/06C09B23/145C09B23/14C07F15/006H01L51/0081Y02E10/549C07F15/0086H10K85/324H10K85/346Y10S428/917
Inventor 埃米尔·侯赛因·帕勒姆阿尔内·比辛安雅·格哈德约阿希姆·凯泽罗科·福特
Owner UDC IRELAND
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